Yes, I know that content in these categories certainly does exist, but the volume is very small compared to many other categories. I am speaking of:
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Bisexual men plus one or more women, with the women receiving anal penetration. Furthermore, the men that perform in this category are mostly a small group. After a while it gets a bit boring that the same man/men are present even if the women are more varied.
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(Cis)-Women receiving anal penetration from trans-women. There is a large volume of transwoman-with-transwoman and transwoman-with-man, but surprisingly few transwoman-with-woman – and, of what I am aware of, the transwoman performers are a fairly small group.
One of the problems I have found when searching for such content is that the sites I have attempted do search on have very limited search terms (imagination?) to specify what I am searching for. No matter how I try to narrow down and be specific in searches, the results almost always come back more general and not the specific categories I have described above.
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I had never thought of that, but I believe you’re right!
The only thing I can think of to help with your searches is to use the actors’ names, which of course comes back to your original problem; limited number. Nevertheless, searching on the known names may lead to discovery of some new names. The chances are new actors to these categories will first appear with the already established names.
Some day I was curious about men having anal sex with transwomen. So I conducted a lot of searches cause to me it was important that the transwoman had a small, useless, limp dick.
A transwoman with a big, hard cock was a big turnoff to me.
I discovered that it’s nearly impossible to find porn with trans women, that don’t have a hard cock the whole fuck ánd get sucked off by the man fucking her. Many times she even starts assfucking him, was was the biggest turnoff of them all.
So yes, the moment you crave for some specific porn, it get’s almost impossible to find it.
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“Bisexual men plus one or more women, with the women receiving anal penetration”
I’ve noticed that most clips in this category, are pretty much all pussy penetration for the women.
I also prefer trans women with a limp, useless dick.
But there is plenty on the internet nowadays, specially on X/Twitter. A lot of men prefer it that way, although a few are attracted to a fully erect penis.
I can show you anytime 
That fase in my life was part of my then unfullfilled sexlife.
Nowdays my sexlife is everything I dreamt of and more, so fullfilled.
The fase passed
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As the original poster, I am curious if anybody has any more thoughts on this topic?
We don’t watch porn that much but when we do, it’s always anal and always amateurs, like us. It’s more raw and realistic.
What‘s more difficult to find are amateur anal videos where the woman experiences an anal orgasm. Her anal orgasms, and my preference for anal, are the reason we’re anal only.
It’s so much more of a turn on when the couple are obviously enjoying their anal sex. Even more of a turn on when the woman has an anal orgasm.